An Ireland-Claisen approach to beta-alkoxy alpha-amino acids.
A diastereoselective Ireland-Claisen approach to beta-alkoxy alpha-amino acid esters is reported. Amino acid esters of enol ethereal allylic alcohols undergo facile syn-selective [3,3]-sigmatropic rearrangement via silyl ketene acetals. Substrate synthesis, rearrangement development, stereoselectivity, and product elaboration are discussed.
Tellam
James P
JP
Department of Chemistry, University of Bath, Bath, UK.
Kociok-Köhn
Gabriele
G
Carbery
David R
DR
D000438:Alcohols / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D000438:Alcohols; D000596:Amino Acids; D004952:Esters; C059688:alkoxyl radical